US6051606A - Pesticidal composition - Google Patents
Pesticidal composition Download PDFInfo
- Publication number
- US6051606A US6051606A US09/368,182 US36818299A US6051606A US 6051606 A US6051606 A US 6051606A US 36818299 A US36818299 A US 36818299A US 6051606 A US6051606 A US 6051606A
- Authority
- US
- United States
- Prior art keywords
- instant invention
- weight
- pesticidal
- pesticidal composition
- glycol monoalkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
- A01N25/06—Aerosols
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
Definitions
- the instant invention relates to pesticidal compositions, and methods of controlling pests.
- South African patent 80-4391 discloses 2-methyl-4-oxo-3-(2-propynyl) cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate as an active ingredient of a pesticide, but 2-methyl-4-oxo-3-(2-propynyl) cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate does not always provide sufficient rapid activity when provided in pesticidal compositions, and more particularly, pesticidal aerosol compositions.
- the rapid activity which is desirous for such compositions should allow a pesticidal composition to control a pest quickly after said pesticidal composition is utilized on said pest.
- Japanese unexamined patent publication No. Hei 2-304004-A discloses propylene glycol monoalkyl ethers and dipropylene glycol dialkyl ethers as active ingredients of a termite-controlling agent.
- the efficacy of the propylene glycol monoalkyl ethers and dipropylene glycol dialkyl ethers in the termite-controlling agent is not satisfactory.
- the instant invention provides a pesticidal composition possessing excellent pesticidal activity and a method of controlling pests.
- the pesticidal compositions of the instant invention possess an unexpectedly superior pesticidal activity when compared with a composition comprising 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate as an active ingredient, without the below glycol derivatives.
- the pesticidal activity in the inventive pesticidal compositions provides a rapid activity, such that the provided pesticidal composition can quickly control a pest after said pest has been exposed to said pesticidal composition.
- the instant invention provides novel pesticidal compositions comprising 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate and a specified glycol derivative, as well as a method of controlling pests which comprises utilizing the inventive pesticidal compositions, wherein the glycol derivative in the pesticidal compositions of the instant invention is a propylene glycol monoalkyl ether, dipropylene glycol monoalkyl ether, or the like.
- a pesticidal composition of the instant invention typically comprises (i) 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate and (ii) a specified glycol derivative, wherein a weight to weight ratio of 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate to the glycol derivative in the pesticidal compositions of the instant invention is preferably about 1:3 to 1:100.
- Suitable glycol derivatives which can be utilized in the pesticidal compositions typically include propylene glycol monoalkyl ethers or dipropylene glycol monoalkyl ethers, and the like.
- the propylene glycol monoalkyl ethers which are utilized in the pesticidal compositions of the instant invention are preferably encompassed by the following formula (I):
- R 1 represents an alkyl group.
- R 1 preferably represents a C 1-4 lower alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl group, or the like, and more preferably an ethyl group or methyl group, and most preferably a methyl group.
- Said propylene glycol monoalkyl ether is most preferably a 1-alkoxy-2-propanol compound, such as 1-methoxy-2-propanol.
- inventive pesticidal compositions comprise a dipropylene glycol monoalkyl ether therein as said glycol derivative
- said dipropylene glycol monoalkyl ether is preferably encompassed by the following formula (II):
- R 2 represents an alkyl group.
- R 2 preferably represents a C 1-4 lower alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl group, or the like, and more preferably an ethyl group, methyl group or the like, and most preferably a methyl group.
- Said dipropylene glycol monoalkyl ethers is most preferably a compound encompassed by the following formula (III) or (IV): ##STR1## wherein R 2 is the same as defined above.
- 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate is generally present in the pesticidal compositions of the instant invention at an amount of from about 0.001 to 30% by weight, based on the total weight of the provided composition.
- Various optical or geometrical isomers thereof may be present in the pesticidal compositions of the instant invention as 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate, provided that said optical or geometrical isomers in the pesticidal compositions of the instant invention are pesticidally active.
- the pesticidal compositions of the instant invention typically comprise the glycol derivative in an amount of from about 0.003 to 99% by weight, and preferably about 0.003 to 91% by weight, based on the total weight of the provided composition.
- the pesticidal compositions of the instant invention are typically produced or formulated by forming a mixture of 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate and a suitable glycol derivative at room temperature or under heated conditions.
- the pesticidal compositions of the instant invention may be produced by additionally dissolving or adding a synergist, fragrance, solvent, solid carrier, other pesticidal compound or the like, into the mixture of 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate and the glycol derivative, if so desired.
- said aerosol composition should typically further comprise a propellant.
- propellants which are utilized in the aerosol formulations of the inventive pesticidal compositions are typically contained therein at an amount of from about 20 to 90% by weight, based on the total weight of the provided composition.
- propellants which may be in the aerosol formulations of the instant invention include propane/butane, dimethyl ether, and the like, or combinations thereof.
- synergists which may be utilized in the pesticidal compositions of the instant invention, if so desired, include PBO, MGK 264, S421, and the like.
- solvents which may be utilized in the pesticidal compositions of the instant invention, if so desired, include kerosene; alkylbenzene such as xylene, trimethyl benzene and dodecylbenzene; diphenyl methanes such as phenylxylylethane; alcohols such as isopropanol; and the like.
- solid carriers which may be utilized in the aerosol formulations of the instant invention, if so desired, include talc, clay, diatomaceous earth, pearlite, gypsum, silica and the like.
- Examples of the other pesticidal compounds which may be utilized in the pesticidal compositions of the instant invention, if so desired, include allethrin, tetramethrin, prallethrin, phenothrin, resmethrin, cyphenothrin, permethrin, cypermethrin, deltamethrin, cyfluthrin, d-furamethrin, imiprothrin, etofenprox, dichlorvos, fenitrothion, propoxur, pyriproxyfen, methoprene, hydroprene, diflubenzuron, cyromazine, and the like.
- inventive methods of controlling pests generally comprise utilizing a pesticidal composition of the instant invention.
- Such methods of the instant invention may utilize an effective amount of the inventive pesticidal compositions for household purposes such as for controlling indoor flies, mosquitoes, cockroaches, ants or the like.
- the methods of the instant invention should typically comprise applying an inventive pesticidal composition to a pest or a locus that the pest inhabits, so that the 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic and the glycol derivative in the composition are applied at a combined amount of from about 0.001 to 10 mg per 1 m 3 of a locus that is being treated therewith.
- the methods of the instant invention should typically comprise applying an inventive pesticidal composition to a pest or a locus that the pest inhabits, so that 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate and the glycol derivative in the composition are applied at a combined amount of from about 0.01 to 100 mg per 1 m 2 of a locus that is being treated therewith.
- the inventive pesticidal compositions can be directly utilized on said pests, or utilized on wood materials or soil which said pests may come in contact therewith.
- the methods of the instant invention may also utilize the inventive pesticidal compositions by diluting said composition, if so desired.
- inventive pesticidal liquid formulation when utilized in the methods of the instant invention, said liquid formulation is diluted so that 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate therein is diluted to a concentration of from about 0.001 to 5% by weight, based on the total weight of the diluted composition.
- pests which are controlled by utilizing the pesticidal compositions of the instant invention include Arthropoda (insects, acarina, and the like) such as Lepidoptera, Diptera, cockroaches (Dictyoptera), Hymenoptera, Siphonaptera, lice (Anoplura), termites (Isoptera), Hemiptera, Coleoptera, thrips (Thysanoptera), Orthoptera, mites or ticks (Acarina), other well known noxious pests or the like.
- Arthropoda insects, acarina, and the like
- Arthropoda insects, acarina, and the like
- Lepidoptera diptera
- cockroaches Dictyoptera
- Hymenoptera Hymenoptera
- Siphonaptera lice
- lice Anoplura
- termites Isoptera
- Hemiptera Hemiptera
- Lepidoptera which are controlled with the methods of the instant invention include Pyralidae such as rice stem borer (Chilo suppressalis), rice leaf roller (Cnaphalocrocis medinalis) and Indian meal moth (Plodia interpunctella), Noctuidae such as tobacco cutworm (Spodoptera litura), rice armyworm (Pseudaletia separata) and cabbage armyworm (Mamestra brassicae), Pieridae such as common cabbageworm (Pieris rape crucivora), Tortricidae such as Adoxophyes spp., Carposinidae, Lyonetiidae, Lymantriidae, agrotis (Agrotis spp.) such as turnip cut worm (Agrothis segetum) and black cutworm (Agrothis ipsilon), Helicovera (Helicovera spp.), heliothis (Heliothis spp.), diamond
- Diptera which are controlled with the methods of the instant invention include mosquitoes such as common mosquito (Culex pipens pallens) and Culex tritaeniorhynchus, Aedes spp. such as yellow fever mosquito (Aedes aegypti) and Aedes alpopictus, Anopheles spp.
- mosquitoes such as common mosquito (Culex pipens pallens) and Culex tritaeniorhynchus
- Aedes spp. such as yellow fever mosquito (Aedes aegypti) and Aedes alpopictus, Anopheles spp.
- Anopheles sinensis and Anopheles stephensi midges (Chironomidae), Muscidae such as housefly (Musca domestica), false housefly (Muscina stabulans) and little housefly (Fannia canicularis), Calliphoridae, Sarcophagidae, Anthomyiidae such as seedcom maggot (Delia platura) and onion maggot (Delia antiqua), fruit flies (Tephritidae), vinegar flies (Drosophilidae), moth flies (Psychodidae), Phoridae, breeze flies (Tabanidae), black flies (Simuliidae), stable flies (Stomoxyidae), biting midges (Ceratopogonidae), and the like.
- Midges Chironomidae
- Muscidae such as housefly (Musca domestica), false housefly (M
- Hymenoptera which are controlled with the methods of the instant invention include ants (Formicidae), hornets/wasps (Vespidae), Bethylidae, sawflies (Tenthredinidae) such as cabbage sawflies (Athalia rosae ruficornis), and the like.
- Siphonaptura which are controlled with the methods of the instant invention include dog fleas (Ctenocephalides canis), cat fleas (Ctenocephalides felis), human fleas (Pulex irritans), and the like.
- More specific examples of the lice (Anoplura) which are controlled with the methods of the instant invention include Pediculus humanus humanus, crab louse (Pthirus pubis), and the like.
- More specific examples of the termites (Isoptera) which are controlled with the methods of the instant invention include Reticulitermes speratus, Formosan subterranean termite (Coptotermes sormosanus), and the like.
- Hemiptera which are controlled with the methods of the instant invention include planthoppers (Delphacidae) such as small brown plant hopper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens) and white-backed rice planthopper (Sogatella furcifera), leafhoppers (Deltocephalidae) such as green rice leafhopper (Nephotettix cincticeps) and green rice leafhopper (Nephotettix virescens), aphids (Aphididae), plant bugs (Heteroptera), whiteflies (Aleyrodidae), scales, lace bugs (Tingidae), jumping plantlice (Psyllidae), Cimicidae, and the like.
- planthoppers (Delphacidae) such as small brown plant hopper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens) and white-backed rice
- Coleoptera which are controlled with the methods of the instant invention include corn rootworms such as black carpet beetle (Attagenus unicolor japonicus), varied carpet beetle (Authrenus verbasci), western corn rootworm (Diabrotica virgifera) and southern corn rootworm (Diabrotica undecimpunctata howardi), scarabs (Scarabaeidae) such as cupreous chafer (Anomala cuprea) and soybean beetle (Anomala rufocuprea), weevils (Curculionidae) such as maize weevil (Sitophilus zeamais), rice water weevil (Lissorhoptrus oryzophilus), ball weevil and adzuki bean weevil (Callosobruchus chinensis), darkling beetles (Tenebrionidae) such as yellow mealworm (Tenebrio molitor) and red flour beetle
- Thrips which are controlled with the methods of the instant invention
- Thrips palmi which are controlled with the methods of the instant invention
- Thrips hawaiiensis More specific examples of the thrips which are controlled with the methods of the instant invention include mole cricket (Gryllotalpa sp.), grasshoppers (Acrididae), and the like.
- insects which are controlled with the methods of the instant invention include spiders (Araneida) such as black widow (Lactrodectus) and Chiracanthium japonicum, millepedes (millipeda), centipedes (centipeda), sow bugs, pill bugs (Armadillida), and the like.
- spiders such as black widow (Lactrodectus) and Chiracanthium japonicum
- millepedes millipeda
- centipedes centipedes
- sow bugs pill bugs (Armadillida), and the like.
- One (1) part by weight of Compound A and 100 parts by weight of propylene glycol monomethyl ether (ARCO Chemical Company, product name: Arcosolv PM) are mixed together at room temperature, to achieve a pesticidal composition of the instant invention.
- One (1) part by weight of Compound A and 10 parts by weight of dipropylene glycol monomethyl ether (ARCO Chemical Company, product name: Arcosolv DPM) are mixed together at room temperature, to achieve a pesticidal composition of the instant invention.
- One (1) part by weight of Compound A and 100 parts by weight of dipropylene glycol monomethyl ether (ARCO Chemical Company, product name: Arcosolv DPM) are mixed together at room temperature, to achieve a pesticidal composition of the instant invention.
- One (1) part by weight of Compound A and 10 parts by weight of propylene glycol monoethyl ether (ARCO Chemical Company, product name: Arcosolv PE) are mixed together at room temperature, to achieve a pesticidal composition of the instant invention.
- One (1) part by weight of Compound A, 10 parts by weight of 1-methoxy-2-propanol and 89 parts by weight of kerosene are mixed together at room temperature, to achieve a pesticidal composition of the instant invention.
- Fifty (50) parts by weight of the pesticidal composition obtained in Formulation Example 6 are packed into an aerosol container. After attaching a valve to the aerosol container, 50 parts by weight of dimethyl ether are charged into the aerosol container through the valve, to achieve a pesticidal composition of the instant invention.
- One (1) part by weight of Compound A and 10 parts by weight of 3-methoxy-3-methyl-1-butanol are mixed together at room temperature, to achieve a pesticidal composition.
- One (1) part by weight of Compound A and 100 parts by weight of 3-methoxy-3-methyl-1-butanol are mixed together at room temperature, to achieve a pesticidal composition.
- One (1) part by weight of Compound A and 10 parts by weight of isopropanol are mixed together at room temperature, to achieve a pesticidal composition.
- One (1) part by weight of Compound A and 100 parts by weight of isopropanol are mixed together at room temperature, to achieve a pesticidal composition.
- One (1) part by weight of Compound A and 10 parts by weight of tripropylene glycol monomethyl ether (ARCO Chemical Company, product name: Arcosolv TPM) are mixed together at room temperature, to achieve a pesticidal composition.
- One (1) part by weight of Compound A and 10 parts by weight of dibutyl phthalate are mixed together at room temperature, to achieve a pesticidal composition.
- One part by weight of Compound A and 100 parts by weight of dibutyl phthalate are mixed together at room temperature, to achieve a pesticidal composition.
- Each of the pesticidal compositions of Formulation Examples 1 to 5 and Comparative Formulation Examples 1 to 7 were diluted with deodorized kerosene so that the concentration of Compound A therein was 0.1% weight/volume.
- a 20 cm ⁇ 20 cm piece of paper was laid over each metal mesh which was set on the bottom area of a 46 cm ⁇ 46 cm ⁇ 70 cm metallic chamber, respectively.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Provided are pesticidal compositions comprising (i) 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate, and (ii) propylene glycol monoalkyl ether or dipropylene glycol monoalkyl ether. In addition, methods of controlling pests which comprise utilizing said composition are provided.
Description
1. Field of the Invention
The instant invention relates to pesticidal compositions, and methods of controlling pests.
2. Description of Related Art
South African patent 80-4391 discloses 2-methyl-4-oxo-3-(2-propynyl) cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate as an active ingredient of a pesticide, but 2-methyl-4-oxo-3-(2-propynyl) cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate does not always provide sufficient rapid activity when provided in pesticidal compositions, and more particularly, pesticidal aerosol compositions. The rapid activity which is desirous for such compositions should allow a pesticidal composition to control a pest quickly after said pesticidal composition is utilized on said pest.
Japanese unexamined patent publication No. Hei 2-304004-A discloses propylene glycol monoalkyl ethers and dipropylene glycol dialkyl ethers as active ingredients of a termite-controlling agent. However, in order to control pests, the efficacy of the propylene glycol monoalkyl ethers and dipropylene glycol dialkyl ethers in the termite-controlling agent is not satisfactory.
The instant invention provides a pesticidal composition possessing excellent pesticidal activity and a method of controlling pests. In this regard, the pesticidal compositions of the instant invention possess an unexpectedly superior pesticidal activity when compared with a composition comprising 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate as an active ingredient, without the below glycol derivatives. For example, the pesticidal activity in the inventive pesticidal compositions provides a rapid activity, such that the provided pesticidal composition can quickly control a pest after said pest has been exposed to said pesticidal composition.
Particularly, the instant invention provides novel pesticidal compositions comprising 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate and a specified glycol derivative, as well as a method of controlling pests which comprises utilizing the inventive pesticidal compositions, wherein the glycol derivative in the pesticidal compositions of the instant invention is a propylene glycol monoalkyl ether, dipropylene glycol monoalkyl ether, or the like.
A pesticidal composition of the instant invention typically comprises (i) 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate and (ii) a specified glycol derivative, wherein a weight to weight ratio of 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate to the glycol derivative in the pesticidal compositions of the instant invention is preferably about 1:3 to 1:100.
Suitable glycol derivatives which can be utilized in the pesticidal compositions typically include propylene glycol monoalkyl ethers or dipropylene glycol monoalkyl ethers, and the like. In such cases, the propylene glycol monoalkyl ethers which are utilized in the pesticidal compositions of the instant invention are preferably encompassed by the following formula (I):
R.sup.1 OC.sub.3 H.sub.6 OH (I)
wherein, R1 represents an alkyl group. Further, in formula (I), R1 preferably represents a C1-4 lower alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl group, or the like, and more preferably an ethyl group or methyl group, and most preferably a methyl group. Said propylene glycol monoalkyl ether is most preferably a 1-alkoxy-2-propanol compound, such as 1-methoxy-2-propanol.
In the event that the inventive pesticidal compositions comprise a dipropylene glycol monoalkyl ether therein as said glycol derivative, said dipropylene glycol monoalkyl ether is preferably encompassed by the following formula (II):
R.sup.2 OC.sub.3 H.sub.6 OC.sub.3 H.sub.6 OH (II)
wherein, R2 represents an alkyl group. Further, in formula (II), R2 preferably represents a C1-4 lower alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl group, or the like, and more preferably an ethyl group, methyl group or the like, and most preferably a methyl group. Said dipropylene glycol monoalkyl ethers is most preferably a compound encompassed by the following formula (III) or (IV): ##STR1## wherein R2 is the same as defined above.
2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate is generally present in the pesticidal compositions of the instant invention at an amount of from about 0.001 to 30% by weight, based on the total weight of the provided composition. Various optical or geometrical isomers thereof may be present in the pesticidal compositions of the instant invention as 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate, provided that said optical or geometrical isomers in the pesticidal compositions of the instant invention are pesticidally active.
The pesticidal compositions of the instant invention typically comprise the glycol derivative in an amount of from about 0.003 to 99% by weight, and preferably about 0.003 to 91% by weight, based on the total weight of the provided composition.
The pesticidal compositions of the instant invention are typically produced or formulated by forming a mixture of 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate and a suitable glycol derivative at room temperature or under heated conditions. Further, the pesticidal compositions of the instant invention may be produced by additionally dissolving or adding a synergist, fragrance, solvent, solid carrier, other pesticidal compound or the like, into the mixture of 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate and the glycol derivative, if so desired. In the event that the inventive pesticidal composition are formulated as an aerosol composition, said aerosol composition should typically further comprise a propellant.
The propellants which are utilized in the aerosol formulations of the inventive pesticidal compositions are typically contained therein at an amount of from about 20 to 90% by weight, based on the total weight of the provided composition. Examples of propellants which may be in the aerosol formulations of the instant invention include propane/butane, dimethyl ether, and the like, or combinations thereof.
Examples of the synergists which may be utilized in the pesticidal compositions of the instant invention, if so desired, include PBO, MGK 264, S421, and the like.
Examples of the solvents which may be utilized in the pesticidal compositions of the instant invention, if so desired, include kerosene; alkylbenzene such as xylene, trimethyl benzene and dodecylbenzene; diphenyl methanes such as phenylxylylethane; alcohols such as isopropanol; and the like.
Examples of solid carriers which may be utilized in the aerosol formulations of the instant invention, if so desired, include talc, clay, diatomaceous earth, pearlite, gypsum, silica and the like.
Examples of the other pesticidal compounds which may be utilized in the pesticidal compositions of the instant invention, if so desired, include allethrin, tetramethrin, prallethrin, phenothrin, resmethrin, cyphenothrin, permethrin, cypermethrin, deltamethrin, cyfluthrin, d-furamethrin, imiprothrin, etofenprox, dichlorvos, fenitrothion, propoxur, pyriproxyfen, methoprene, hydroprene, diflubenzuron, cyromazine, and the like.
The inventive methods of controlling pests generally comprise utilizing a pesticidal composition of the instant invention. Such methods of the instant invention may utilize an effective amount of the inventive pesticidal compositions for household purposes such as for controlling indoor flies, mosquitoes, cockroaches, ants or the like. In cases in which the pesticidal compositions are utilized to control flying insects such as flies, mosquitoes or the like, the methods of the instant invention should typically comprise applying an inventive pesticidal composition to a pest or a locus that the pest inhabits, so that the 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic and the glycol derivative in the composition are applied at a combined amount of from about 0.001 to 10 mg per 1 m3 of a locus that is being treated therewith. In cases in which the inventive compositions are utilized to control crawling insects such as cockroaches, ants or the like, the methods of the instant invention should typically comprise applying an inventive pesticidal composition to a pest or a locus that the pest inhabits, so that 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate and the glycol derivative in the composition are applied at a combined amount of from about 0.01 to 100 mg per 1 m2 of a locus that is being treated therewith.
For example, in the event of controlling pests of wood materials such as Reticulitermes speratus, Formosan subterranean termite or the like, the inventive pesticidal compositions can be directly utilized on said pests, or utilized on wood materials or soil which said pests may come in contact therewith.
The methods of the instant invention may also utilize the inventive pesticidal compositions by diluting said composition, if so desired. Typically, when an inventive pesticidal liquid formulation is utilized in the methods of the instant invention, said liquid formulation is diluted so that 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate therein is diluted to a concentration of from about 0.001 to 5% by weight, based on the total weight of the diluted composition.
Examples of pests which are controlled by utilizing the pesticidal compositions of the instant invention include Arthropoda (insects, acarina, and the like) such as Lepidoptera, Diptera, cockroaches (Dictyoptera), Hymenoptera, Siphonaptera, lice (Anoplura), termites (Isoptera), Hemiptera, Coleoptera, thrips (Thysanoptera), Orthoptera, mites or ticks (Acarina), other well known noxious pests or the like. More specific examples of the Lepidoptera which are controlled with the methods of the instant invention include Pyralidae such as rice stem borer (Chilo suppressalis), rice leaf roller (Cnaphalocrocis medinalis) and Indian meal moth (Plodia interpunctella), Noctuidae such as tobacco cutworm (Spodoptera litura), rice armyworm (Pseudaletia separata) and cabbage armyworm (Mamestra brassicae), Pieridae such as common cabbageworm (Pieris rape crucivora), Tortricidae such as Adoxophyes spp., Carposinidae, Lyonetiidae, Lymantriidae, agrotis (Agrotis spp.) such as turnip cut worm (Agrothis segetum) and black cutworm (Agrothis ipsilon), Helicovera (Helicovera spp.), heliothis (Heliothis spp.), diamondback moth (Plutella xylostella), rice skipper (Parnara guttata), casemaking clothes moth (Tinea pellinella), webbing clothes moth (Tineola bisselliella), Indian meal moth (Plodia interpunctella), oriental moth (Monema flavescens), oriental tussock moth (Euproctis subflava), and the like. More specific examples of the Diptera which are controlled with the methods of the instant invention include mosquitoes such as common mosquito (Culex pipens pallens) and Culex tritaeniorhynchus, Aedes spp. such as yellow fever mosquito (Aedes aegypti) and Aedes alpopictus, Anopheles spp. such as Anopheles sinensis and Anopheles stephensi, midges (Chironomidae), Muscidae such as housefly (Musca domestica), false housefly (Muscina stabulans) and little housefly (Fannia canicularis), Calliphoridae, Sarcophagidae, Anthomyiidae such as seedcom maggot (Delia platura) and onion maggot (Delia antiqua), fruit flies (Tephritidae), vinegar flies (Drosophilidae), moth flies (Psychodidae), Phoridae, breeze flies (Tabanidae), black flies (Simuliidae), stable flies (Stomoxyidae), biting midges (Ceratopogonidae), and the like. More specific examples of the cockroaches which are controlled with the methods of the instant invention include German cockroach (Blattella germanica), smoky brown cockroach (Periplaneta fuliginosa), American cockroach (Periplaneta americana), brown cockroach (Periplaneta brunnea), Oriental cockroach (Blatta orientalis), and the like. More specific examples of the Hymenoptera which are controlled with the methods of the instant invention include ants (Formicidae), hornets/wasps (Vespidae), Bethylidae, sawflies (Tenthredinidae) such as cabbage sawflies (Athalia rosae ruficornis), and the like. More specific examples of the Siphonaptura which are controlled with the methods of the instant invention include dog fleas (Ctenocephalides canis), cat fleas (Ctenocephalides felis), human fleas (Pulex irritans), and the like. More specific examples of the lice (Anoplura) which are controlled with the methods of the instant invention include Pediculus humanus humanus, crab louse (Pthirus pubis), and the like. More specific examples of the termites (Isoptera) which are controlled with the methods of the instant invention include Reticulitermes speratus, Formosan subterranean termite (Coptotermes sormosanus), and the like. More specific examples of the Hemiptera which are controlled with the methods of the instant invention include planthoppers (Delphacidae) such as small brown plant hopper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens) and white-backed rice planthopper (Sogatella furcifera), leafhoppers (Deltocephalidae) such as green rice leafhopper (Nephotettix cincticeps) and green rice leafhopper (Nephotettix virescens), aphids (Aphididae), plant bugs (Heteroptera), whiteflies (Aleyrodidae), scales, lace bugs (Tingidae), jumping plantlice (Psyllidae), Cimicidae, and the like. More specific examples of the Coleoptera which are controlled with the methods of the instant invention include corn rootworms such as black carpet beetle (Attagenus unicolor japonicus), varied carpet beetle (Authrenus verbasci), western corn rootworm (Diabrotica virgifera) and southern corn rootworm (Diabrotica undecimpunctata howardi), scarabs (Scarabaeidae) such as cupreous chafer (Anomala cuprea) and soybean beetle (Anomala rufocuprea), weevils (Curculionidae) such as maize weevil (Sitophilus zeamais), rice water weevil (Lissorhoptrus oryzophilus), ball weevil and adzuki bean weevil (Callosobruchus chinensis), darkling beetles (Tenebrionidae) such as yellow mealworm (Tenebrio molitor) and red flour beetle (Tribolium castaneum), leaf beetles (Chrysomelidae) such as rice leaf beetle (Oulema oryzae), striped flea beetle (Phyllotreta striolata) and cucurbit leaf beetle (Aulacophora femoralis), deathwatch beetles (Anobiidae), Epilachna (Epilachna spp.) such as twenty-eight-spotted ladybird (Epilachna Vigintioctopunctata), powderpost beetles (Lyctidae), lesser grain borers (Rhizopertha dominica), beet tortoise beetles (Cassida nebulosa), robe beetles (Paederus fuscipes), and the like. More specific examples of the thrips (Thysanoptera) which are controlled with the methods of the instant invention include Thrips palmi, western flower thrips, flower thrips (Thrips hawaiiensis), and the like. More specific examples of the Orthoptera which are controlled with the methods of the instant invention include mole cricket (Gryllotalpa sp.), grasshoppers (Acrididae), and the like. More specific examples of the mites or ticks which are controlled with the methods of the instant invention include Dermanyssidae such as American house dust mite, Dermatophagoides frarinae and Dermatophagoides pteronyssinus, Acaridae such as mold mite (Tyrophagus putrescentiae) and brown legged grain mite (Aleuroplyphus ovatus), Glycyphagidae such as Glycyphagus privatus, Glycyphagus domesticus and Glycyphagus destructor, Cheyletidae such as Chelacaropsis malaccensis, Cheyletus fortis and Chelacaropsis moorei, Tarsonemidae, chortoglyphus spp., Halplochthonis simplex, spider mites (Tetranychidae) such as two-spotted spider mite (Tetranychus urticae), Kanzawa spider mite (Tetranychus kanzawai), citrus red mite (Panonychus citri) and European red mite (Panochychus ulmi), Ixodidae such as Haemaphxalis longicornis, and the like. More specific examples of the other pests which are controlled with the methods of the instant invention include spiders (Araneida) such as black widow (Lactrodectus) and Chiracanthium japonicum, millepedes (millipeda), centipedes (centipeda), sow bugs, pill bugs (Armadillida), and the like.
Hereinafter, the instant invention is explained in further detail through the examples, but the instant invention is not limited to the examples.
One (1) part by weight of (S)-2-methyl-4-oxo-3-(2-propynyl) cyclopent-2-enyl (1R)-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (hereinafter referred to as Compound A) and 10 parts by weight of propylene glycol monomethyl ether (ARCO Chemical Company, product name: Arcosolv PM) are mixed together at room temperature, to achieve a pesticidal composition of the instant invention.
One (1) part by weight of Compound A and 100 parts by weight of propylene glycol monomethyl ether (ARCO Chemical Company, product name: Arcosolv PM) are mixed together at room temperature, to achieve a pesticidal composition of the instant invention.
One (1) part by weight of Compound A and 10 parts by weight of dipropylene glycol monomethyl ether (ARCO Chemical Company, product name: Arcosolv DPM) are mixed together at room temperature, to achieve a pesticidal composition of the instant invention.
One (1) part by weight of Compound A and 100 parts by weight of dipropylene glycol monomethyl ether (ARCO Chemical Company, product name: Arcosolv DPM) are mixed together at room temperature, to achieve a pesticidal composition of the instant invention.
One (1) part by weight of Compound A and 10 parts by weight of propylene glycol monoethyl ether (ARCO Chemical Company, product name: Arcosolv PE) are mixed together at room temperature, to achieve a pesticidal composition of the instant invention.
One (1) part by weight of Compound A, 10 parts by weight of 1-methoxy-2-propanol and 89 parts by weight of kerosene are mixed together at room temperature, to achieve a pesticidal composition of the instant invention.
Five (5) parts by weight of Compound A, 15 parts by weight of 1-ethoxy-2-propanol and 80 parts by weight of kerosene are mixed together at room temperature, to achieve a pesticidal composition of the instant invention.
Fifty (50) parts by weight of the pesticidal composition obtained in Formulation Example 6 are packed into an aerosol container. After attaching a valve to the aerosol container, 50 parts by weight of dimethyl ether are charged into the aerosol container through the valve, to achieve a pesticidal composition of the instant invention.
Two (2) parts by weight of 1-ethoxy-2-propanol and 0.10 parts by weight of Compound A, 9.9 parts by weight of an anhydrous silica, and 2 parts by weight of isopropyl myristate are packed into an aerosol container. After attaching a valve to the aerosol container, 86 parts by weight of dimethyl ether are charged into the aerosol container through the valve, to achieve an aerosol formulation of the instant invention.
One (1) part by weight of Compound A and 10 parts by weight of 3-methoxy-3-methyl-1-butanol are mixed together at room temperature, to achieve a pesticidal composition.
One (1) part by weight of Compound A and 100 parts by weight of 3-methoxy-3-methyl-1-butanol are mixed together at room temperature, to achieve a pesticidal composition.
One (1) part by weight of Compound A and 10 parts by weight of isopropanol are mixed together at room temperature, to achieve a pesticidal composition.
One (1) part by weight of Compound A and 100 parts by weight of isopropanol are mixed together at room temperature, to achieve a pesticidal composition.
One (1) part by weight of Compound A and 10 parts by weight of tripropylene glycol monomethyl ether (ARCO Chemical Company, product name: Arcosolv TPM) are mixed together at room temperature, to achieve a pesticidal composition.
One (1) part by weight of Compound A and 10 parts by weight of dibutyl phthalate are mixed together at room temperature, to achieve a pesticidal composition.
One part by weight of Compound A and 100 parts by weight of dibutyl phthalate are mixed together at room temperature, to achieve a pesticidal composition.
Each of the pesticidal compositions of Formulation Examples 1 to 5 and Comparative Formulation Examples 1 to 7 were diluted with deodorized kerosene so that the concentration of Compound A therein was 0.1% weight/volume.
A 20 cm×20 cm piece of paper was laid over each metal mesh which was set on the bottom area of a 46 cm×46 cm×70 cm metallic chamber, respectively. A container wherein said container had a diameter of 8.75 cm, a height of 7.5 cm, 5 male and 5 female German cockroaches present therein, a 16 mesh metal mesh overlaid on the bottom area thereof, as well as butter spread on the wall surfaces thereof, was deposited onto each of said 20 cm×20 cm piece of papers.
Three-quarters milliliters (0.75 mL) of the diluted pesticidal compositions were then sprayed from above said chambers, respectively, in the direction of the cockroaches, at a pressure of 0.42 kg/cm2, and by use of a spray gun. Each of the containers was removed from the chambers 30 seconds thereafter, and the German cockroaches were transferred into plastic cups. The time needed to knock down the German cockroaches in each of the plastic cups was examined. The tests were performed at least 2 times. The averages of the results are shown in Table 1.
TABLE 1 ______________________________________ The Time needed to knockdown all the insects Test Example # The Pesticidal Oily Composition (minutes) ______________________________________ 1 Formulation Example 1 3 2 Formulation Example 2 3 3 Formulation Example 3 5 4 Formulation Example 4 5 5 Formulation Example 5 1.5 Comparative 1 Comparative Formulation Example 1 more than 10 Comparative 2 Comparative Formulation Example 2 more than 10 Comparative 3 Comparative Formulation Example 3 more than 10 Comparative 4 Comparative Formulation Example 4 more than 10 Comparative 5 Comparative Formulation Example 5 more than 10 Comparative 6 Comparative Formulation Example 6 more than 10 Comparative 7 Comparative Formulation Example 7 more than 10 ______________________________________
The results of the above test and comparative examples evidence that the pesticidal compositions of the instant invention provide an excellent pesticidal activity and that the removal of the glycol derivative therefrom or the use of another solvent does not result in such surprisingly advantageous results.
Each of the patent documents and publications that are mentioned in the instant specification are incorporated herein by reference in their entirety.
Claims (10)
1. A pesticidal composition comprising:
(i) 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate, and
(ii) a propylene glycol monoalkyl ether or a dipropylene glycol monoalkyl ether.
2. The pesticidal composition according to claim 1, wherein a weight to weight ratio of (i) 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate to (ii) the propylene glycol monoalkyl ether or the dipropylene glycol monoalkyl ether in said pesticidal composition is from 1:3 to 1:100.
3. The pesticidal composition according to claim 1, wherein the composition comprises:
(i) 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate, and
(ii) the propylene glycol monoalkyl ether.
4. The pesticidal composition according to claim 1, wherein the composition comprises:
(i) 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate, and
(ii) the dipropylene glycol monoalkyl ether.
5. The pesticidal composition according to claim 3, wherein the propylene glycol monoalkyl ether is a propylene glycol monomethyl ether or propylene glycol monoethyl ether.
6. The pesticidal composition according to claim 4, wherein the dipropylene glycol monoalkyl ether is a dipropylene glycol monomethyl ether.
7. The pesticidal composition according to claim 1, wherein the composition further comprises a propellant.
8. The pesticidal composition according to claim 1, wherein the composition further comprises a propellant and a solid carrier.
9. A method of controlling pests which comprises applying an effective amount of a pesticidal composition comprising:
(i) 2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate, and
(ii) a propylene glycol monoalkyl ether or a dipropylene glycol monoalkyl ether to a pest or a locus where the pest inhabits.
10. The method according to claim 9, wherein the pest is a cockroach.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10-225763 | 1998-08-10 | ||
JP10225763A JP2000053512A (en) | 1998-08-10 | 1998-08-10 | Insecticidal composition |
Publications (1)
Publication Number | Publication Date |
---|---|
US6051606A true US6051606A (en) | 2000-04-18 |
Family
ID=16834435
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/368,182 Expired - Fee Related US6051606A (en) | 1998-08-10 | 1999-08-04 | Pesticidal composition |
Country Status (9)
Country | Link |
---|---|
US (1) | US6051606A (en) |
JP (1) | JP2000053512A (en) |
KR (1) | KR20000017232A (en) |
CN (1) | CN1244345A (en) |
AR (1) | AR020146A1 (en) |
BR (1) | BR9903567A (en) |
ES (1) | ES2164549B1 (en) |
FR (1) | FR2781984A1 (en) |
IT (1) | IT1307264B1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007002988A1 (en) * | 2005-06-30 | 2007-01-11 | Microbial Products Pty Ltd | Formulation of microbial pesticides |
WO2008123571A2 (en) * | 2007-03-30 | 2008-10-16 | Sumitomo Chemical Company, Limited | Pesticidal composition and method for controlling harmful insects |
US20130172409A1 (en) * | 2010-09-09 | 2013-07-04 | Sumitomo Chemical Company, Limited | Pest controlling method, composition, electrostatic spray device and use thereof |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4231894B1 (en) * | 2008-03-31 | 2009-03-04 | 大日本除蟲菊株式会社 | Spray for controlling houseflies |
JP5550938B2 (en) * | 2010-02-18 | 2014-07-16 | 住友化学園芸株式会社 | Aerosol composition for slaughter |
CN108697077B (en) * | 2015-09-25 | 2022-04-19 | 组合块公司 | Polyol, carbohydrate, nucleobase and nucleoside compositions and uses thereof |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5620546A (en) * | 1979-07-27 | 1981-02-26 | Sumitomo Chem Co Ltd | Carboxylic acid ester |
US4473582A (en) * | 1980-08-14 | 1984-09-25 | Zoecon Corporation | Insecticidal stick applicator and method |
JPS6284001A (en) * | 1985-10-09 | 1987-04-17 | Nippon Nohyaku Co Ltd | Aerosol agricultural chemical composition |
JP2855724B2 (en) * | 1989-11-29 | 1999-02-10 | 住友化学工業株式会社 | Aerosol insecticide |
DE19620891A1 (en) * | 1996-05-23 | 1997-11-27 | Paul Habich | Agent for hygiene or materials protection from flying or crawling insects |
-
1998
- 1998-08-10 JP JP10225763A patent/JP2000053512A/en active Pending
-
1999
- 1999-08-04 US US09/368,182 patent/US6051606A/en not_active Expired - Fee Related
- 1999-08-09 ES ES009901821A patent/ES2164549B1/en not_active Withdrawn - After Issue
- 1999-08-09 BR BR9903567-7A patent/BR9903567A/en not_active IP Right Cessation
- 1999-08-09 IT IT1999TO000702A patent/IT1307264B1/en active
- 1999-08-10 AR ARP990103984A patent/AR020146A1/en not_active Application Discontinuation
- 1999-08-10 CN CN99117710A patent/CN1244345A/en active Pending
- 1999-08-10 FR FR9910354A patent/FR2781984A1/en active Pending
- 1999-08-10 KR KR1019990032800A patent/KR20000017232A/en not_active Application Discontinuation
Non-Patent Citations (2)
Title |
---|
Arthur and E. Rose (The condensed Medical Dictionary, Sixth Edition, p. 409, Reinold Publishing Corporation, New York), 1963. * |
Tanaka Y. et al. (CA 127:105644, abstract of JP 09177915), 1997. * |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007002988A1 (en) * | 2005-06-30 | 2007-01-11 | Microbial Products Pty Ltd | Formulation of microbial pesticides |
WO2008123571A2 (en) * | 2007-03-30 | 2008-10-16 | Sumitomo Chemical Company, Limited | Pesticidal composition and method for controlling harmful insects |
WO2008123571A3 (en) * | 2007-03-30 | 2009-09-17 | Sumitomo Chemical Company, Limited | Pesticidal composition and method for controlling harmful insects |
US8173702B2 (en) | 2007-03-30 | 2012-05-08 | Sumitomo Chemical Company, Limited | Pesticidal composition and method for controlling harmful insects |
RU2455824C2 (en) * | 2007-03-30 | 2012-07-20 | Сумитомо Кемикал Компани, Лимитед | Pesticide composition and pest control method |
US20130172409A1 (en) * | 2010-09-09 | 2013-07-04 | Sumitomo Chemical Company, Limited | Pest controlling method, composition, electrostatic spray device and use thereof |
Also Published As
Publication number | Publication date |
---|---|
ITTO990702A1 (en) | 2001-02-09 |
FR2781984A1 (en) | 2000-02-11 |
AR020146A1 (en) | 2002-04-10 |
ES2164549B1 (en) | 2003-06-16 |
ITTO990702A0 (en) | 1999-08-09 |
KR20000017232A (en) | 2000-03-25 |
JP2000053512A (en) | 2000-02-22 |
IT1307264B1 (en) | 2001-10-30 |
ES2164549A1 (en) | 2002-02-16 |
CN1244345A (en) | 2000-02-16 |
BR9903567A (en) | 2000-09-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE69906014T2 (en) | Pyrethroid compounds and pest control compositions containing them | |
BR0300949B1 (en) | 4-METOXYMETHYL-2,3,5,6-TETRAFLUOROBENZYL 2-ClANO-1-PROPENYL-2,2-DIMETHYLTHYCYLOCROPANOCARBOXYL ESTER COMPOSITE, PESTICIDE COMPOSITION AND PEST CONTROL METHOD | |
RU2358971C2 (en) | Pyrethroid pesticide | |
KR101520978B1 (en) | Pesticidal composition and method for controlling harmful insects | |
AU685609B2 (en) | Compositions for the inhibition of protein hormone formation and uses thereof | |
AU2008222039B2 (en) | Pesticidal composition and method for controlling a pest | |
EP2670246B1 (en) | Pesticidal composition and method for controlling pests | |
WO2008123573A2 (en) | Pesticidal aerosol composition | |
AU8956898A (en) | Ester compound and pesticide containing thereof | |
US6051606A (en) | Pesticidal composition | |
US7662988B2 (en) | Ester compound and its use | |
EP0959065B1 (en) | Pyrethroid compound and composition for controlling pest containing the same | |
US4985457A (en) | Novel carboxylic acid esters, methods for producing them and insecticides and/or acaricides containing them as an active ingredient | |
US5055491A (en) | Carboxylic acid esters, methods for producing them and insecticides and/or acaricides containing them as an active ingredient | |
US6423745B1 (en) | Pyrethroid compound and composition for controlling pest containing the same as an active ingredient | |
US5019595A (en) | Novel carboxylic acid esters and insecticides containing them as an active ingredient | |
EP1625792B1 (en) | Pesticidal composition | |
US5607963A (en) | Maleimide pesticides and compositions thereof | |
AU8515198A (en) | Ester compound and pesticide containing thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: SUMITOMO CHEMICAL COMPANY, LIMITED, JAPAN Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:TANAKA, YASUYORI;ISHIWATARI, TAKAO;REEL/FRAME:010153/0631 Effective date: 19990624 |
|
REMI | Maintenance fee reminder mailed | ||
LAPS | Lapse for failure to pay maintenance fees | ||
FP | Lapsed due to failure to pay maintenance fee |
Effective date: 20040418 |
|
STCH | Information on status: patent discontinuation |
Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362 |